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Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife

Holiday home in St. Michaels with kitchen

Photo gallery for Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife

Fridge, microwave, oven, stovetop - Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife (St. Michaels)
Exterior - Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife (St. Michaels)
Exterior detail - Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife (St. Michaels)
3 bedrooms, free WiFi, bed sheets - Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife (St. Michaels)
Property grounds - Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife (St. Michaels)
In historic St. Michaels, Carpenter Alley Cottage offers the perfect blend of charm and modern conveniences. Enjoy nearby access to top-rated restaurants, boutiques, art galleries and waterfront activities like freshly caught steamed crabs along the Miles River.

Reviews

9.8 out of 10
Exceptional

Entire home

3 bedrooms3 bathroomsSleeps 6119 sq m

Popular amenities

  • Kitchen
  • Washing machine
  • Dryer
  • Free Wi-Fi
  • Air-conditioning

Add dates for prices

About this property

Entire place

You'll have the entire home to yourself and will only share it with other guests in your party.

Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife

Cottage in Center of Historic St. Michaels

This lovely in-town cottage is close to all the amenities and charms of historic St. Michaels. Enjoy outstanding restaurants and boutiques, ice cream parlors, coffee shops, art galleries and more, all within a few steps of this beautiful home! Try the local winery, distillery, and brewery for tastings of hand-crafted spirits (no driving required!).

Head toward the Miles River waterfront for freshly caught and steamed crabs. If you want to venture farther, within just a couple of blocks you can easily rent bikes, kayaks, or paddleboards and let your adventurous side soar. Offering modern conveniences in a quintessential Eastern Shore village, Carpenter Alley Cottage is a fabulous place to stay!

PROPERTY FEATURES:

Pet Policy: This is a pet friendly rental.
Grill: Propane grill. Propane is provided.
WiFi: Please note that the rural nature of the area may limit data access. Some of our properties can experience slow internet speeds.

BED SIZES:

Bunk Bed - Single over Single - 1 / Queen - 1 / Queen - 1 / Queen - 1 /

Property amenities

Internet

  • Available in the house: Free WiFi

Parking and transport

  • Parking on site

Kitchen

  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Hob
  • Microwave
  • Oven
  • Refrigerator
  • Toaster

Dining

  • Dining table

Bedrooms

  • 3 bedrooms
  • Bedsheets provided

Bathroom

  • 3 bathrooms
  • Towels provided

Living spaces

  • Dining table
  • Living room

Entertainment

  • TV

Outdoor areas

  • Barbecue grill
  • Fenced yard
  • Garden

Laundry

  • Laundry facilities
  • Washing machine

Comfort

  • Air conditioning
  • Heating

Pets

  • Pet friendly

Suitability/Accessibility

  • Smoke-free property

Location highlights

  • In a village
  • Near a health/beauty spa
  • Near a hospital
  • Near an outlet shopping centre

Things to do

  • Fishing nearby
  • Golfing nearby
  • Kayaking nearby
  • Motor boating nearby
  • Sailing nearby
  • Swimming nearby
  • Wildlife walks nearby
  • Winery tours nearby

Safety features

  • Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
  • Smoke detector (host has indicated there is a smoke detector on the property)

General

  • Garden
  • Unit size: 1,280 square feet

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  • Kitchen
  • Washing machine
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Policies

Check-in

Check-in time starts at 4:00 PM
Minimum check-in age - 25

Check-out

Check-out before 10:00 AM

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions
Information provided by the property may be translated using automated translation tools

Pets

Pets are allowed
Service animals are welcome, and are exempt from fees

Children and extra beds

Children are welcome

Events

No events allowed

Smoking

Smoking is not permitted

Important information

You need to know

Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation

Property is also known as

Vrbo Property
18

About the area

Map
St. Michaels, MD

What's nearby

  • Higgins Yacht Yard and Marina - 2 min walk - 0.2 km
  • St. Michaels Marina - 3 min walk - 0.3 km
  • Chesapeake Bay Maritime Museum - 6 min walk - 0.6 km
  • 1879 Hooper Straight Lighthouse - 6 min walk - 0.6 km
  • St. Michaels Winery - 8 min walk - 0.7 km

Getting around

  • Cambridge Station - 33 min drive
  • Easton, MD (ESN-Easton - Newnam) - 20 min drive

Restaurants

  • ‪Stars - ‬10 min walk
  • ‪Foxy's Harbor Grille - ‬4 min walk
  • ‪The Crab Claw - ‬6 min walk
  • ‪Carpenter Street Saloon - ‬1 min walk
  • ‪Ava's Pizzeria & Wine Bar - St Michaels - ‬4 min walk

Frequently asked questions

Is Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife pet-friendly?

Yes, pets are allowed at this property.

How much is parking at Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife?

On-site parking is available at the property.

What time is check-in at Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife?

Check-in begins at 4:00 PM.

What time is check-out at Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife?

Checkout is at 10:00 AM.

Where is Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife located?

Located in Downtown St. Michaels, this holiday home is steps away from Higgins Yacht Yard and Marina and Muskrat Park. St. Michaels Marina and Saint Marys Square Museum are also within 10 minutes.

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Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife Reviews

Reviews

Exceptional

All reviews shown are from real guest experiences. Only travellers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative.
More informationOpens in a new window
Rating 10 - Excellent. 41 out of 46 reviews
Rating 8 - Good. 4 out of 46 reviews
Rating 6 - Okay. 1 out of 46 reviews
Rating 4 - Poor. 0 out of 46 reviews
Rating 2 - Terrible. 0 out of 46 reviews

10

Cleanliness

9.8

Location

Reviews

10/10 Excellent

Jennifer E.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Conveniently located!
Stayed 3 nights in Aug 2025

10/10 Excellent

Glen H.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Perfect location, everything as advertised. Highly recommend
Stayed 3 nights in Sep 2025

10/10 Excellent

Sydney S.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Wonderful home in excellent location!!
Stayed 7 nights in May 2025

10/10 Excellent

Jerome K.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Nice house perfectly located

Good location, clean house, easy check in and check out process.
Stayed 2 nights in May 2025

10/10 Excellent

Lanise M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great location and great house

Property was perfect for our family stay. House was clean and well stocked.
Stayed 3 nights in Apr 2025

10/10 Excellent

Josh M.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Very clean and modern house in excellent location in downtown St. Michael’s. Very comfortable and included convenient parking.
Stayed 3 nights in Jun 2025

10/10 Excellent

Davinia W.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Amazing location

Great location with two parking spots and a small yard. Great for family vacation.
Stayed 2 nights in Mar 2025

10/10 Excellent

Cindi W.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Girls’ Weekend

We had a wonderful weekend in St. Michaels and our stay at ur Carpenter Alley address was clean, nicely decorated, and the location was perfect for our group!
Stayed 2 nights in May 2025

10/10 Excellent

Katie m.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect location

The house was beautiful and location perfect. Would definitely stay again!
Stayed 2 nights in May 2023

10/10 Excellent

Rennie M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Girls Trip

Perfect for a 3 day visit!
Stayed 3 nights in Jul 2024

8/10 Good

Ferne D.

Liked: Cleanliness, check-in, communication, location, listing accuracy

St. Michaels

Very clean, great location
Stayed 2 nights in Sep 2024

10/10 Excellent

Scott B.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Location walking distance to everything, house well maintained, fenced back yard. The only thing that should be upgraded is upstairs air conditioning. We could not get inside temperature below 79 F on hot days. Maybe upsize capacity. Downstairs cooling was good.
Stayed 3 nights in Aug 2025

10/10 Excellent

Audra B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Awesome girls weekend!

This cottage is adorable. Great amenities and great location. We thoroughly enjoyed our time in St Michael’s.
Stayed 2 nights in Jan 2023

10/10 Excellent

Karen L.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect place!

The house was perfect for our needs. It has a cute, fenced in yard so our 2 dogs could hang outside. It had everything we needed for a wonderful weekend birthday celebration!
Stayed 2 nights in May 2024

8/10 Good

Karen E.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Location, location, location

We were able to walk to most places we wanted to go in town. The house was a little small but everything we needed was there and the property managers were easy to reach. We had a great time!
Stayed 3 nights in Oct 2024

10/10 Excellent

Brett H.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect Location to Downtown St. Michael's

The stay was a perfect location for doing things in downtown St. Michael's, everything is within walking distance. The property managers were prompt with all communications and pleasant to work with on a few questions I had.
Stayed 2 nights in May 2024

10/10 Excellent

Saum S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

St. Michael's

Amazing location in the middle of everything
Stayed 3 nights in Aug 2023

10/10 Excellent

Mark C.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Bright space in a great location

If you you want to spend time walking around St. Michaels, this is the perfect spot, right in the middle of town. The three bedrooms are all comfortable, and the kitchen/living room is a nice place to hang out.
Stayed 5 nights in Dec 2022

10/10 Excellent

Justin D.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great House/Great Location!

Our family really enjoyed our time. The location of the house could not be better, just a few steps off of the main street! The house was very nice. Would definitely return!
Stayed 3 nights in Mar 2023

10/10 Excellent

Amy B., Pineville USA

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect House

This was the perfect house in the perfect location for our visit to St. Michael’s. The house was very clean and having a bedroom on the first floor was wonderful for our older guests. Hope to return.
Stayed 2 nights in Oct 2023

10/10 Excellent

Sarah Z.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Waterfowl

We had a great stay at this property this year. Great location in town, and wonderful outdoor space for our dog as well. Very clean and ESVR provided all the items you need for the stay. Everyone had a good time for our long weekend stay for the Waterfowl festival.
Stayed 3 nights in Nov 2023

10/10 Excellent

Vicki P.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great choice.

Loved the house. It was clean and pretty. Fabulous location.
Stayed 3 nights in Jun 2019

10/10 Excellent

Wes T., Annapolis, MD

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great location!

House was very clean, comfortable and well laid out. The location is fantastic! Perfect for being immersed in downtown Saint Michael’s. We’re able to walk to everything. Have the dog with us what a nice bonus.
Stayed 2 nights in May 2023

10/10 Excellent

Tom O.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great central location in St Michaels

Carpenter Alley was the perfect place for our group of family friends to explore St Michaels and the Eastern Shore. Right off the main street, an easy walk to all that St Michaels has to offer. Plenty of room for 6 adults with a great sized kitchen, upstairs and downstairs seating areas and fenced in back yard. Highly recommend.
Stayed 3 nights in Jun 2024

10/10 Excellent

Dia S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Very nice property, well located.

Property manager was helpful and very responsive. The property was very clean and tidy, but a bit sterile.
Stayed 3 nights in Nov 2022